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Regio- and stereoselective synthesis of functionalized and fused heterocycles from Morita-Baylis-Hillman adducts of dicyclopentadienone
Journal
Organic and Biomolecular Chemistry
ISSN
14770520
Date Issued
2022-02-24
Author(s)
Suresh, Alati
Lal, Sohan
Namboothiri, Irishi N.N.
Abstract
An efficient protocol for the Morita-Baylis-Hillman (MBH) reaction of dicyclopentadienone using CTAB has been developed. The MBH adduct was subsequently transformed to its acetate and bromide derivatives. The 1,3-bielectrophilic character of the MBH acetate and bromide was further explored with various 1,3-binucleophiles to construct various oxa-, thia- and aza-heterocycles. These reactions proceed through a cascade double Michael addition of 1,3-binucleophiles to the MBH acetate/bromide under basic conditions. Amenability of these reactions to scale-up and applications of the products in the synthesis of cyclopentenone-fused chromenones and thiopyranoindoles have been demonstrated.